$200 Find Cheap Flights from Hawaii to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Fri, May 22 - Sun, May 31
Delta Logo
9:55 pm - 1:54 pm
LIH
-
ORD
10h 59m
1 stop
Delta Logo
12:47 pm - 7:06 pm
ORD
-
LIH
11h 19m
1 stop
$474Delta
Thu, Aug 20 - Wed, Aug 26
Delta Logo
9:55 pm - 1:41 pm
KOA
-
ORD
10h 46m
1 stop
Delta Logo
7:00 am - 5:35 pm
ORD
-
KOA
15h 35m
1 stop
$494Delta
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$500Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
12:35 pm - 6:22 am
KOA
-
ORD
12h 47m
1 stop
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$524Alaska Airlines
Fri, May 22 - Sun, May 31
American Airlines Logo
9:51 pm - 2:21 pm
LIH
-
ORD
11h 30m
1 stop
American Airlines Logo
6:00 am - 8:21 pm
ORD
-
LIH
19h 21m
1 stop
$534American Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
12:35 pm - 6:22 am
KOA
-
ORD
12h 47m
1 stop
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$544Alaska Airlines
Fri, Oct 16 - Sun, Oct 25
American Airlines Logo
11:14 pm - 4:03 pm
HNL
-
ORD
11h 49m
1 stop
American Airlines Logo
9:45 am - 2:00 pm
ORD
-
HNL
9h 15mnonstop
$545American Airlines
Thu, Aug 20 - Wed, Aug 26
Southwest Logo
8:35 pm - 12:05 pm
KOA
-
MDW
10h 30m
1 stop
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
$569Southwest
Thu, Aug 20 - Wed, Aug 26
Southwest Logo
7:05 pm - 1:20 pm
KOA
-
MDW
13h 15m
2 stops
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
$575Southwest
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
9:00 am - 7:32 pm
ORD
-
KOA
15h 32m
2 stops
$580Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$200
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.